Irresistibly Sweet Pineapple Upside-Down Cupcakes Recipe

Sweet pineapple upside-down cupcakes bring nostalgic memories of grandma’s kitchen to life with a delightful twist.

Tropical flavors dance through each golden-brown morsel, creating a miniature dessert that feels both classic and contemporary.

Buttery caramelized fruit nestles perfectly atop tender cake, promising a delectable bite every single time.

Compact and charming, these individual treats eliminate the hassle of cutting traditional large cakes.

Moist crumb meets glistening fruit in a compact package that screams summer celebration.

Professional bakers and home cooks alike will adore how simple yet impressive these little delights can be.

Come discover a recipe that turns ordinary afternoons into memorable moments of pure culinary joy.

Pineapple Upside-Down Cupcakes: A Tropical Classic Reimagined

• Rescue Classic Dessert: Transform the traditional pineapple upside-down cake into adorable, individual cupcake portions that are perfect for personal servings.
• Elevate Presentation: Create stunning mini desserts with a gorgeous caramelized pineapple and cherry topping that looks professionally crafted and delivers a wow factor for any gathering.
• Master Bakery-Style Treat: Achieve professional-looking cupcakes with minimal baking skills, using simple ingredients and straightforward steps that guarantee delicious results every single time.
• Versatile Party Pleaser: Delight guests at potlucks, birthdays, and family celebrations with these charming cupcakes that blend nostalgic flavors with modern presentation.

Essential Ingredients for Pineapple Upside-Down Cupcakes

• Butter: Provides a rich, smooth base for the caramelized sugar coating.
• Brown Sugar: Creates a sweet, sticky caramel layer that adds depth to the cupcake.
• Pineapple Rings: Offers a tangy, tropical fruit element to the dessert.
• Maraschino Cherries: Adds a bright pop of color and sweet flavor to the topping.

• All-Purpose Flour: Forms the structural base of the cupcake.
• Baking Powder, Baking Soda: Helps the cupcake rise and become light and fluffy.
• Salt: Enhances the overall flavor of the cupcake.

• Butter, Granulated Sugar: Creates a creamy, sweet foundation for the cake batter.
• Eggs: Provides structure and helps bind the ingredients together.
• Vanilla Extract: Adds a warm, classic flavor to the cupcakes.
• Pineapple Juice, Buttermilk: Brings moisture and tanginess to the cake batter.

Step-by-Step Pineapple Upside-Down Cupcakes Magic

Step 1: Fire Up the Oven

Crank your oven to 350F (175C). Grab a 12-cup muffin tin and give it a quick spray of cooking oil or line it with cupcake liners.

Step 2: Create the Sticky Sweet Base

• Melted butter
• Brown sugar

Scoop about a teaspoon of this golden mixture into each muffin cup. Gently place a halved pineapple ring on top, pressing it softly into the sugary goodness.

Drop a bright maraschino cherry right in the center of each pineapple ring.

Step 3: Mix the Magical Cake Batter

• All-purpose flour
• Baking powder
• Baking soda
• Salt

In a separate large bowl, cream the butter and granulated sugar until they’re light and fluffy.

Crack in the eggs one by one, mixing thoroughly after each. Splash in the vanilla extract for extra flavor.

Step 4: Combine Wet and Dry Ingredients

Slowly fold the dry ingredients into the butter mixture. Pour in pineapple juice and buttermilk, alternating between dry and wet ingredients.

Mix just until everything comes together – don’t overwork the batter!

Step 5: Fill and Prepare for Baking

Carefully spoon the batter into each muffin cup, filling them about three-quarters full.

Make sure to cover the pineapple and cherry base completely.

Step 6: Bake to Golden Perfection

Slide the muffin tin into the preheated oven.

Bake for 20-25 minutes. Check doneness by inserting a toothpick into the center – it should come out clean.

Step 7: Flip and Reveal the Treasure

Let the cupcakes rest in the pan for 5 minutes. Place a wire rack or large baking sheet over the tin.

With a confident motion, flip the pan to release the cupcakes. Watch as the caramelized pineapple and cherry topping dramatically reveals itself!

Step 8: Cool and Serve

Allow the cupcakes to cool completely. The anticipation will be worth the wait!

These treats are perfect for sharing with friends or enjoying as a special personal indulgence.

Pro Tips for Pineapple Upside-Down Cupcakes Success

• Generously grease the muffin tin or use high-quality non-stick liners to ensure easy cupcake removal and perfect pineapple topping presentation.
• Use room temperature eggs and buttermilk to create a smoother, more evenly mixed batter that results in tender, soft cupcakes.
• Insert a toothpick at a slight angle into the cupcake's center; if it comes out with just a few moist crumbs, the cupcakes are perfectly baked.
• Let cupcakes rest for exactly 5 minutes before inverting, allowing the caramel topping to set slightly and prevent breaking during release.

Creative Variations on Pineapple Upside-Down Cupcakes

• Tropical Paradise: Replace pineapple rings with mango slices and coconut flakes for a Caribbean-inspired version.
• Rum Runner: Add a tablespoon of dark rum to the cake batter and sprinkle toasted coconut on top for an adult-friendly treat.
• Berry Bliss: Swap pineapple with caramelized strawberries and add a hint of almond extract for a fruity summer cupcake.
• Spiced Autumn: Mix ground cinnamon and nutmeg into the batter, top with caramelized apples instead of pineapple for a seasonal spin.

Best Pairings for Pineapple Upside-Down Cupcakes

• Pair with Tropical Rum Cocktail: Mix light rum, pineapple juice, and a splash of coconut cream for a refreshing drink that echoes the cupcake's tropical flavors.
• Complement with Vanilla Bean Ice Cream: Serve a scoop of creamy vanilla bean ice cream alongside the cupcake to balance the caramelized sweetness and provide a cool contrast.
• Match with Toasted Coconut Sprinkle: Garnish the cupcake or plate with toasted coconut flakes to enhance the tropical profile and add a delightful crunch.
• Serve with Chai Latte: The warm spices in a chai latte create a wonderful counterpoint to the sweet, fruity cupcake, offering a complex flavor experience.

How to Store Pineapple Upside-Down Cupcakes Properly

• Wrap individual cupcakes in plastic wrap or store in an airtight container for up to 3-4 days. Keep them cool and away from strong-smelling foods to preserve their delicate flavor.
• Place cupcakes in a freezer-safe container, separating layers with parchment paper. Freeze for up to 2 months. Thaw overnight in the refrigerator before serving.
• Let cupcakes sit at room temperature for 2 hours maximum. Cover loosely with a clean kitchen towel to prevent drying out.

FAQs

• Can I use fresh pineapple instead of canned rings?

Yes, you can use fresh pineapple rings. Just ensure they’re cut to a similar size as the canned rings and pat them dry to prevent excess moisture.

• What if I don't have buttermilk?

Make a quick buttermilk substitute by adding 1 tablespoon of white vinegar or lemon juice to 1 cup of milk. Let it sit for 5 minutes before using.

• Can I make these cupcakes ahead of time?

Absolutely! You can bake these cupcakes a day in advance. Store them in an airtight container at room temperature and they’ll stay moist and delicious.

Pineapple Upside-Down Cupcakes Recipe

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4.7 from 16 reviews

• Total Time: 45 minutes
• Yield: 12 1x

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Description

Sweet pineapple upside-down cupcakes bring classic dessert charm into perfectly portioned individual treats. Caramelized fruit topping and moist golden cake create a delightful tropical twist you’ll absolutely love.

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Ingredients

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Fruit and Pineapple Components:

• 6 canned pineapple rings, halved
• 12 maraschino cherries
• 1/2 cup (120ml) pineapple juice

Cake Base Ingredients:

• 1 1/2 cups (190g) all-purpose flour
• 3/4 cup (150g) granulated sugar
• 1/2 cup (115g) unsalted butter, softened
• 1/2 cup (120ml) buttermilk
• 2 large eggs
• 1 teaspoon baking powder
• 1/2 teaspoon baking soda
• 1/4 teaspoon salt
• 1 teaspoon vanilla extract

Topping Ingredients:

• 1/4 cup (60g) unsalted butter, melted
• 1/2 cup (100g) light brown sugar

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Instructions

1. Prepare the oven environment at 350F (175C) and ready a 12-cup muffin tin with grease or liner.

1. Craft the caramelized foundation by blending melted butter and brown sugar. Distribute approximately one teaspoon of this luxurious mixture into each muffin cavity.

1. Nestle a halved pineapple ring into each cup, gently pressing it into the sugary base. Position a vibrant maraschino cherry at the heart of each pineapple ring.

1. Create the cake base by whisking flour, baking powder, baking soda, and salt in a separate bowl. In a larger vessel, cream butter and granulated sugar until airy and voluminous.

1. Incorporate eggs individually, ensuring thorough integration after each addition. Introduce vanilla extract for depth of flavor.

1. Gradually fold dry ingredients into the mixture, alternating with pineapple juice and buttermilk. Mix delicately to maintain the batter’s ethereal texture.

1. Carefully ladle batter over the pineapple-cherry arrangement, filling each cup approximately three-quarters full.

1. Slide the muffin tin into the preheated oven, baking for 20-25 minutes until a toothpick emerges pristine when inserted into the cupcake’s center.

1. Allow cupcakes to rest in the pan for five minutes, then invert onto a wire rack or baking sheet, revealing the caramelized topping.

1. Permit cupcakes to cool completely, transforming into a delectable dessert ready to enchant eager palates.

Notes

• Swap out buttermilk with dairy-free alternatives like almond milk mixed with apple cider vinegar for a vegan-friendly version.
• Room temperature ingredients ensure smoother batter and more even baking, helping cupcakes rise consistently.
• Line muffin cups with extra parchment paper for easier removal and cleaner edges when flipping the cupcakes.
• Drain maraschino cherries thoroughly to prevent excess liquid from affecting the caramel topping’s texture.

• Prep Time: 20 minutes
• Cook Time: 25 minutes
• Category: Desserts
• Method: Baking
• Cuisine: American

Nutrition

• Serving Size: 12
• Calories: 211 kcal
• Sugar: 21 g
• Sodium: 129 mg
• Fat: 10 g
• Saturated Fat: 6 g
• Unsaturated Fat: 4 g
• Trans Fat: 0.3 g
• Carbohydrates: 29 g
• Fiber: 0.5 g
• Protein: 2.5 g
• Cholesterol: 45 mg